Hello Gatorgal -
I don't know where in Flordia you are currently living especially if it is a bigger city but, I can see why your husband is nervous. I spent quiet a bit of time in Chitown years ago and loved it. I'm originally from NYC and NC is very different then the big cities like Chicago and NYC. There are things I miss but I love the open air here.
You may want to look at the North Davidson County Area - close to W-S but, lower property taxes. This is a fast growing area and I have only heard high praises about the schools.
I have put several links to schools in NC, Forsyth/W-S , and Davidson county schools.
North Carolina Public Schools
North Carolina Public Schools
Forsyth/ Winston-Salem Public Schools mts.admin.wsfcs.k12.nc.us
Davidson County Schools
www.davidson.k12.nc.us
I hope that helps - Good Luck - and a little premature but welcome to NC.